3-(cyclohex-1-enyl)-4-iodo-1-methoxy-1H-isochromene | 587882-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(cyclohex-1-enyl)-4-iodo-1-methoxy-1H-isochromene
• 英文别名: 1H-2-Benzopyran, 3-(1-cyclohexen-1-yl)-4-iodo-1-methoxy-；3-(cyclohexen-1-yl)-4-iodo-1-methoxy-1H-isochromene
• CAS: 587882-47-1
• 化学式: C₁₆H₁₇IO₂
• 分子量: 368.214
• InChiKey: WVAIJGBECQOLCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-乙炔基环己烷 在 palladium catalyst copper(l) iodide 、 碘 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(cyclohex-1-enyl)-4-iodo-1-methoxy-1H-isochromene
  参考文献：
  名称：

  Syntheses of Isochromenes and Naphthalenes by Electrophilic Cyclization of Acetylenic Arenecarboxaldehydes

  摘要：

  Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I-2, ICI, NIS, Br-2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with 12 and simple olefins or alkynes.

  DOI：

  10.1021/jo0524573

文献信息

• The Reaction ofo-Alkynylarene and Heteroarene Carboxaldehyde Derivatives with Iodonium Ions and Nucleophiles: A Versatile and Regioselective Synthesis of 1H-Isochromene, Naphthalene, Indole, Benzofuran, and Benzothiophene Compounds
  作者：José Barluenga、Henar Vázquez-Villa、Isabel Merino、Alfredo Ballesteros、José M. González

  DOI：10.1002/chem.200501505

  日期：2006.7.24

  adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives (23, 27, and 28, respectively). The three patterns of reactivity observed for the o-alkynylbenzaldehyde derivatives with IPy(2)BF(4) stem from a common iodinated isobenzopyrylium ion intermediate, A, that evolves in a different way depending on the nucleophile present in the reaction medium. A mechanism is proposed

  邻炔基苯甲醛1与不同的醇，甲硅烷基化的亲核试剂5，富电子芳烃10和杂芳烃12在试剂IPy（2）BF（4）的存在下在室温下反应，得到官能化的4-碘-1H -异丁烯2、6、11和13以区域选择性的方式。当炔烃16和烯烃19和20用作亲核试剂时，发生区域选择性的苯并环化反应，分别形成1-碘代萘17和1-萘基酮18。而且，后一种方法已经适应于完成吲哚，苯并呋喃和苯并噻吩衍生物的合成（分别为23、27和28）。观察到的邻炔基苯甲醛衍生物与IPy（2）BF（4）的三种反应模式源自共同的碘化异苯并吡啶离子中间体A 取决于反应介质中存在的亲核试剂，其以不同的方式进化。提出了一种机理，并讨论了根据亲核试剂类型观察到的不同反应途径。此外，通过NMR光谱监测邻己基苯甲醛1b与苯乙烯的反应。已分离出化合物III，它是不存在酸时常见中间体的静止状态。还已经测试了其在酸性介质中的演化，从而为提出的机制提供了支持。分离
• Cyclization of Carbonyl Groups onto Alkynes upon Reaction with IPy₂BF₄ and Their Trapping with Nucleophiles:  A Versatile Trigger for Assembling Oxygen Heterocycles
  作者：José Barluenga、Henar Vázquez-Villa、Alfredo Ballesteros、José M. González

  DOI：10.1021/ja0355372

  日期：2003.7.1

  Iodonium ions liberated from bis(pyridine)iodonium(I) tetrafluoroborate react with ortho-alkynyl-substituted carbonyl compounds and different nucleophiles to give valuable iodinated heterocycles at room temperature, through a new and metal-free reaction sequence. Interestingly, the nature of the nucleophile can be widely modified, and not only alcohols but also several carbon-based nucleophiles can

  从双（吡啶）碘鎓（I）四氟硼酸盐释放的碘鎓离子与邻炔基取代的羰基化合物和不同的亲核试剂在室温下通过新的无金属反应序列反应生成有价值的碘化杂环。有趣的是，亲核试剂的性质可以被广泛修改，不仅可以很好地使用醇，还可以很好地使用几种碳基亲核试剂。
• Efficient Syntheses of Heterocycles and Carbocycles by Electrophilic Cyclization of Acetylenic Aldehydes and Ketones
  作者：Dawei Yue、Nicola Della Cà、Richard C. Larock

  DOI：10.1021/ol049690s

  日期：2004.5.1

  substituted oxygen heterocycles can be prepared in good yields at room temperature by reacting o-(1-alkynyl)-substituted arene carbonyl compounds with NBS, I(2), ICl, p-O(2)NC(6)H(4)SCl, or PhSeBr and various alcohols or carbon-based nucleophiles. Naphthyl ketones and iodides are readily prepared by the reaction of 2-(1-alkynyl)arene-carboxaldehydes with I(2) and simple olefins or alkynes.

  通过使邻-（1-炔基）-取代的芳烃羰基化合物与NBS，I（2），ICl，pO（2）NC（6）H（4）SCl反应，可以在室温下以高收率制备高度取代的氧杂环，PhSeBr和各种醇或碳基亲核试剂。萘甲酮和碘化物可通过2-（1-炔基）芳烃-甲醛与I（2）和简单的烯烃或炔烃的反应制备。
• Syntheses of Isochromenes and Naphthalenes by Electrophilic Cyclization of Acetylenic Arenecarboxaldehydes
  作者：Dawei Yue、Nicola Della Cá、Richard C. Larock

  DOI：10.1021/jo0524573

  日期：2006.4.1

  Highly substituted 1H-isochromenes, isobenzofurans, and pyranopyridines can be prepared by allowing o-(1-alkynyl)arenecarboxaldehydes and ketones to react with I-2, ICI, NIS, Br-2, NBS, p-O2NC6H4SCl, or PhSeBr and various alcohols or carbon-based nucleophiles at room temperature. Naphthyl ketones and iodides are also readily prepared by the reaction of 2-(1-alkynyl)arenecarboxaldehydes with 12 and simple olefins or alkynes.